Ossipee Holiday Rentals

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Our top choices for Ossipee holiday rentals

Rustic Rose Cottage of Historic West Lebanon

Rustic Rose Cottage of Historic West Lebanon
Lebanon
10.0 out of 10, Exceptional, (25 reviews)
"Everything about our stay was lovely! Check-in was smooth, the property was gorgeous, and the cottage was full of charm. "
United States
Daniel S.
The price is NZ$383
includes taxes & fees
13 Apr - 14 Apr
Rustic Rose Cottage of Historic West Lebanon

1 of 2 Enchanting 1 room cabins in Shapleigh, ME located on sloaping forest land

1 of 2 Enchanting 1 room cabins in Shapleigh, ME located on sloaping forest land
Shapleigh
9.0 out of 10, Wonderful, (4 reviews)
"Stayed for 2 nights and had a wonderful relaxing time. Very kind and repsonsive hosts. We especially loved the fire pit. Would stay again in a heart beat. "
United States
Bethany K.
The price is NZ$270
includes taxes & fees
30 Apr - 1 May
1 of 2 Enchanting 1 room cabins in Shapleigh, ME located on sloaping forest land

Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard

Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
Wolfeboro
9.6 out of 10, Exceptional, (11 reviews)
"Excellent stay"
United States
Kara
The price is NZ$295
includes taxes & fees
16 Apr - 17 Apr
Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard

Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!

Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
Alton
10.0 out of 10, Exceptional, (1 review)
"This is a classic old-style cabin that reminded us of our childhood family trips in the 60’s. It’s not new, but a heck of a lot of fun if you’re in the right head space. Easily walked to town for dinner and to the shore. Clean and had everything we needed."
United States
Christine F.
The price is NZ$390
includes taxes & fees
8 May - 9 May
Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!

Inviting condo in quiet locale with partial lake views, balcony & grilling area

Inviting condo in quiet locale with partial lake views, balcony & grilling area
Gilford
8.4 out of 10, Very good, (17 reviews)
"Everything was just as listed, full amenities and cleanliness."
United States
John C.
The price is NZ$450
includes taxes & fees
17 Apr - 18 Apr
Inviting condo in quiet locale with partial lake views, balcony & grilling area

Lotus Spa, your home away from home

Lotus Spa, your home away from home
Acton
10.0 out of 10, Exceptional, (50 reviews)
"This place has thought of absolutely everything to make it a cozy and relaxing stay "
United States
Cara L.
The price is NZ$492
includes taxes & fees
14 Apr - 15 Apr
Lotus Spa, your home away from home

Adorable Cabin with stunning lake views & Now featuring AC Wi-FI and TV access

Adorable Cabin with stunning lake views & Now featuring AC Wi-FI and TV access
Alton
9.2 out of 10, Wonderful, (7 reviews)
"We had an amazing stay, adorable area, loved the access to the lake and kayaking, close to great options for outdoor place. Looking forward to future trips"
United States
Amy S.
The price is NZ$346
includes taxes & fees
9 May - 10 May
Adorable Cabin with stunning lake views & Now featuring AC Wi-FI and TV access

Waterfront w/ Prvt Dock & Firepit | Sleeps 8

Waterfront w/ Prvt Dock & Firepit | Sleeps 8
Acton
9.6 out of 10, Exceptional, (15 reviews)
"Love the area & location on the lake!"
United States
Will M.
The price is NZ$1,005
includes taxes & fees
16 Apr - 17 Apr
Waterfront w/ Prvt Dock & Firepit | Sleeps 8

Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard

Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard
Wolfeboro
10.0 out of 10, Exceptional, (17 reviews)
"This is a great place to stay with a dog"
United States
David M.
The price is NZ$303
includes taxes & fees
12 Apr - 13 Apr
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard

Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette

Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette
Alton
9.0 out of 10, Wonderful, (22 reviews)
"Great little gem given its price, location, and overall accommodations! "
United States
Kevin R.
The price is NZ$486
includes taxes & fees
1 May - 2 May
Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette

Dog Friendly, Quiet Neighborhood, Cozy lower level cabin

Dog Friendly, Quiet Neighborhood, Cozy lower level cabin
Conway
10.0 out of 10, Exceptional, (95 reviews)
"The notes are helpful. Easy check in and out. The house is clean and cozy."
United States
Tessie
The price is NZ$402
includes taxes & fees
26 Apr - 27 Apr
Dog Friendly, Quiet Neighborhood, Cozy lower level cabin

Rufus III Yurt on the river

Rufus III Yurt on the river
Brownfield
10.0 out of 10, Exceptional, (12 reviews)
"Had a great time,will be back for sure. "
United States
John C.
The price is NZ$316
includes taxes & fees
12 Apr - 13 Apr
Rufus III Yurt on the river

Grandmas Cottage on the River and the Rail Trail in Wolfeboro

Grandmas Cottage on the River and the Rail Trail in Wolfeboro
Wolfeboro
10.0 out of 10, Exceptional, (18 reviews)
"We had the best time here, would 100% go back. Very quiet and relaxing and the hosts were great."
United States
The F.
The price is NZ$1,032
includes taxes & fees
16 Apr - 17 Apr
Grandmas Cottage on the River and the Rail Trail in Wolfeboro

Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
Alton
8.6 out of 10, Excellent, (18 reviews)
"Nice location on the lake."
United States
Mary L.
The price is NZ$538
includes taxes & fees
9 May - 10 May
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

White Mountains Waterfront Chalet w/ Private Beach

White Mountains Waterfront Chalet w/ Private Beach
Eidelweiss Village
9.8 out of 10, Exceptional, (25 reviews)
"Beautiful home facing the lake. Perfect for a family getaway! "
United States
Navin W.
The price is NZ$747
includes taxes & fees
19 Apr - 20 Apr
White Mountains Waterfront Chalet w/ Private Beach

Cozy three bedroom house located just five minutes from Lake Winnipesaukee

Cozy three bedroom house located just five minutes from Lake Winnipesaukee
Wolfeboro
8.0 out of 10, Very good, (17 reviews)
"Thanks for a great stay!"
United States
Lynne Q.
The price is NZ$583
includes taxes & fees
12 Apr - 13 Apr
Cozy three bedroom house located just five minutes from Lake Winnipesaukee

Great Conway Location! Shop Eat Hike Swim

Great Conway Location! Shop Eat Hike Swim
Settlers Green
7.8 out of 10, Good, (26 reviews)
"Room was clean enough, but the location in the midst of a outlet mall left a lot to be desired for a stop on a leaf peeping vacation."
United States
Kelly C.
The price is NZ$366
includes taxes & fees
12 Apr - 13 Apr
Great Conway Location! Shop Eat Hike Swim

Perfect Modern Lake Front Retreat with Dock! Sleeps 4

Perfect Modern Lake Front Retreat with Dock! Sleeps 4
Alton
9.4 out of 10, Exceptional, (25 reviews)
"Great visit and property as described! Clean, all inclusive, and would recommend. View was beautiful and had a wonderful time."
United States
Catherine M.
The price is NZ$711
includes taxes & fees
12 Apr - 13 Apr
Perfect Modern Lake Front Retreat with Dock! Sleeps 4

Ava Jade yurt nestled in the woods of Brownfield, Maine

Ava Jade yurt nestled in the woods of Brownfield, Maine
Brownfield
10.0 out of 10, Exceptional, (19 reviews)
"Beautiful , clean , secluded Yurt . We truly enjoyed our stay "
United States
Judy S.
The price is NZ$279
includes taxes & fees
12 Apr - 13 Apr
Ava Jade yurt nestled in the woods of Brownfield, Maine

Stunning Lake Views close to Weirs Beach & Gunstock

Stunning Lake Views close to Weirs Beach & Gunstock
Weirs Beach
The price is NZ$345
includes taxes & fees
11 May - 12 May
Stunning Lake Views close to Weirs Beach & Gunstock
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Ossipee Hotel Reviews

Find out more about Ossipee

Everything you need to know about Ossipee holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Ossipee holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ossipee holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Ossipee holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ossipee. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Ossipee holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Ossipee holiday rentals we have selected for you start as low as NZ$827 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Ossipee rentals

At Expedia, we put the best Ossipee holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Ossipee rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ossipee holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ossipee. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Ossipee?

Yes, there are holiday rentals close to the most popular sights in Ossipee, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Ossipee has to offer?

Waterfront cabin near Fish Cove with private dock, water access, firepit, grill: This holiday home rental outside of Ossipee is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Ossipee?

With 7 Expedia holiday rentals, you're guaranteed to find just the right place for your Ossipee stay.

What’s there to see and do in Ossipee?

While exploring the area, visit family-friendly sights like Kellerhaus, or get outside and enjoy nature at Lake Winnipesaukee. In the wider area, you’ll find Ossipee Lake Trail and Lake Wentworth.

What’s a holiday rental in Ossipee like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Ossipee. Holiday rentals offer amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for families.